


Confessional Torture

by HeroFizzer



Category: RWBY
Genre: Bondage, Collars, Femdom, Leather, Multi, Other, Pegging
Language: English
Status: Completed
Published: 2020-10-06
Updated: 2020-10-06
Packaged: 2021-03-07 16:42:10
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,569
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26850859
Author URL: https://archiveofourown.org/users/HeroFizzer/pseuds/HeroFizzer
Summary: It's pretty clear to Nora that Ruby and Oscar like each other. However, it's tough to get either of them to spit it out. So naturally, Valkyrie can't help herself, deciding to put them through a little 'session' to finally spill the beans.
Relationships: Oscar Pine/Ruby Rose
Kudos: 10





	Confessional Torture

**Author's Note:**

> The following story was won in a raffle in celebration of reaching 1k followers on Twitter.
> 
> If you'd like to be apart of another raffle in the future, please be sure to follow me in the link at the end of the story.

“...And then I said, 'Now that's a katana!' and then I kept reading and...”

“Ruby! You tell that story all the time!”

As they walked along the campus of Haven Academy, Ruby was remarking on an incident back at Beacon with Nora. The two had managed to get along well after their journey from Beacon, but it was still never a fully perfect experience, given how the group was trying to gel following the loss of Pyrrha. Then, of course, the rest of RWBY joined them at Haven, which threw off the remaining JNPR members and their own dynamic.

“So what's wrong with that? It's a fun story to tell!”

“You tell it like, every time there's about to be some kind of shenanigans going on! Isn't there anything else a bit more particular you'd want to talk about? Like what happened in classes today, maybe?”

“Well...”

“Ruby, hey!” Just as Ruby was contemplating how her day had been going, they were approached by Oscar. The young man was heading their way, carrying the walking stick he awkwardly had on him.

“Oh, Oscar! Hey! So, um, what's up?” Ruby asked, a huge smile going from ear to ear across her face.

“You know...not too much,” Oscar said as he rubbed the back of his head. “I just saw you guys walking around and thought, oh hey, it's Ruby. And ah...Nora, of course! So I figured I might as well come and say hi to you!”

As the two were talking, Nora felt as though she was being ignored by the pair, even if Oscar had actually bothered to mention her by name. She couldn't help but notice that there was something between the two, unspoken words that nobody else had thought to say. The redhead cackled to herself, awaiting their split before she continued to speak to the RWBY leader.

“Well...I gotta go! Just gotta go off to, um, place...” Oscar said, his face turning bright red.

“Right, yeah! Okay, sure, we gotta go, too!” Ruby said, failing to subdue her excitement. “Seeya, Oscar!”

After they walked away from the young farm boy, Nora couldn't help but cackle louder, finally getting the attention of the young Rose. “What, what's so funny?” Ruby asked.

“Nothing!” Nora said, despite the shit-eating grin she had. “Nothing at all...”

“C'mon, spill it!” whined Ruby.

“It's just cute, don't you think?” Nora asked. “You, Oscar, you guys obviously have a crush on one another!”

“Uh, ha, is it that obvious?” Ruby asked, covering one of her cheeks with her hand. “I mean, I'm sure it's obvious on my end, but I dunno about Oscar...”

Nora let out a loud laugh, one she had been holding back for the last few minutes. “What do you MEAN you don't know about Oscar?!” she asked, causing Ruby to try and shush her so that Oscar couldn't hear them even as he was quite a distance away from them. “Did you see how he looks at you? How he was ALSO awkwardly fumbling to say something other than dead silence!”

“...No?” Ruby said, her eyes shifting about.

“Geez, you can't possibly be that dense, Ruby! Even for you!”

Ruby shrugged. “I guess I'm just worried that he might not show those feelings back, is all...” Ruby admitted.

“For the love of...” Nora sighed, deciding not to press further.

##

“Nora, hi, is this seat taken?”

The redheaded huntress looked up to see Oscar with a pile of books, though she looked around in curiosity. It wasn't as if there were other places in the library to sit at, and there was one in particular she was ready to point out.

“I guess, but what abou-”

“Great, thanks!” Oscar said, immediately sitting next to Nora. “I feel like I'd get a lot more work done sitting next to you.”

“Thhhhhanks...?” Nora said, uncertain if that was a compliment or insult. She looked back at another table in the space, glancing at Ruby while she was studying diligently on her schoolwork. “Hey, aren't you and Ruby working on the same subject? Why don't you go and talk to her, maybe you guys can compare notes or something.”

That was when Oscar's cheeks lit up, his lips thinning as he looked away from Nora. “Well, I mean, I could, but I just worry about saying the wrong thing to her.”

“Why? You like her, don't you?” Nora asked.

“I do, and I know she likes me...I guess that’s more clear than I’d like it to be,” he said, tapping away at his noggin, “but I just chicken out at the last minute when I try to tell her that.”

Nora groaned, slamming her head on the table top. “You two are dorks...” she said to herself. With a sigh, Nora went back to her own work, though she had these talks with Ruby and Nora in the back of her mind. She was going to do something about these two for sure.

##

“Uh, okay, Nora, what did you want me to dress like this for...?”

Ruby stepped into the training area of Haven, a trench coat over her form. She had walked in feeling uncomfortable with herself as if what she wore underneath didn't suit her. Worse off, when she entered the room, she saw Nora standing before her, yet she wasn't alone. Ruby jumped as she saw Oscar was right there as well while the redhead put a collar around his throat. The farm boy wore very little, having on a corset that exposed his chest and cock, letting the huntress see just how hung he was, as well as a pair of high heel latex boots.

“R-Ruby?!” Oscar squeaked, tugging on the collar as it fit around his throat. “Nora, I thought you were asking me to be your only slave to learn how to talk to Ruby better.”

“Wait, that's what she told you?!” Ruby asked, removing her trench coat to reveal she was wearing a similar outfit as what Oscar had on. “She told ME she wanted me to be her slave!”

Nora cackled to herself, fixing up her corset so that it covered up her chest. “Boy, you two are so gullible!” laughed the redhead. “You seriously thought I did this to train you to confess your love better? I just wanted to whip you into shape to actually confess it to each other!” She then pulled out a whip, cracking it in the air to get the attention of the pair, with both startled by the sudden noise. Oscar almost lost balance in his boots, not used to the nine inch heel it provided. “Now get on your knees! And get together! I don't want any distance between you!”

As Nora showed off her dominant side, Ruby and Oscar cowered as they knelt next to one another. Either of them could have said no to this, but it seemed as though they were so desperate to actually sputter out the words that they wanted to say the most to one another. Seeing her new toys in place, Nora began to buckle a harness around her pelvis, with a huge ten-inch cock on the end. She was at least polite enough to cover it in lube, though it still made the farmboy clench his sphincter as he thought about where it would go.

“On all fours! Now!” Nora said, cracking her whip. The two did just that, with Oscar seemingly presenting his ass higher to the mistress out of an instinct even he had no idea he had.It was as if he actually enjoyed the idea of having something shoved up his ass.

“Well, I see one of you's more eager than the other,” Nora laughed, rubbing the lube into the toy shaft, “I think I'll give it to you first, Oscar.” She then proceeded to push the lubed tip against his asshole, hearing him whimper as it prepared to push through, even if he was still clenching in. He then bared his clenched teeth together, his irises shrinking as Ruby watched on. His anus was being pegged by their red-haired friend, the thick tool making its way up her rectum.

“That feels...weirdly good...” Oscar groaned, his mouth drooling as Nora pushed the toy deeper within his rectal cavity. “Can you push deeper?”

“It can only go so far,” Nora assured him, with her crotch meeting with his ass, “but I appreciate you wanting to try and get it deeper.” She then proceeded to pump away at his ass, with the balls of the cock hitting against his taint rather hard. His own member was throbbing underneath, swinging in the air with every jut made by the huntress.

Ruby watched on, sucking her lower lip as she waited for her chance. As she bucked into Oscar's rear, she let go of her whip, instead grabbing a multi-strand crop that she used for Ruby's small but bubbly rear. The black haired huntress yelped as the multiple strands cracked into her backside, raising the skin to a swelling point. Ruby shivered as she curled her chin against her chest, shivering from the repeated smacks by the device.

“N-Nora, how does this help us...?” Ruby soon asked, her tongue hanging from her mouth when the whipping came to a stop.

“Honestly, it's just an excuse to beat you two for being so dumb and dense,” Nora grunted as she pumped her toy cock harder inside Oscar's rectum, “but I figure this should loosen you two up enough that you should finally be able to get the words out of your mouths!”

She then held out the handle of the crop out to Ruby's mouth, prompting the huntress to bite down on it, which she did so. The black haired huntress had no idea if she should use it while it was between her teeth, though she admitted it was something nice to chew on while she witnessed her crush being pegged by a cock. Oscar then tensed up, his back arching as he unleashed his seed on the floor of the training room. It was an embarrassing sight for him, to be sure, especially since his own crush saw him get off to having a dick up his ass, but it also felt relieving at the same time.

Nora pulled out as Oscar panted, moving onto Ruby next. She was more than willing to put the same toy she had up his ass inside her pussy, especially as she saw her fellow huntress grow wet from the previous pegging. “Doesn't it turn you on, Ruby, seeing your boy toy be treated like he's mine?” Nora cackled, rubbing the tip against her folds while using the vaginal fluids to lube her up once again. “Maybe with enough training I can make him yours instead.”

The black haired girl tried to speak with the crop in her mouth, though it came out surprisingly clear what she was saying, “I-I don't know if I could be like tha-haaaaaat...” Ruby's words were interrupted as Nora shoved the shaft inside the huntress, her folds spreading far enough that her canal would soon stretch thanks to the thickness of the dildo. Her teeth bit down hard on the handle of the crop, only for the redhead to take it back soon after.

As Ruby was reamed by the shaft, her bubbly rear shaking after every thrust, Nora used the crop to smack Oscar's ass, hearing him yelp in a high-pitched tone while rocking his body back and forth. It was as though he were trying to fan off the pain of the bondage equipment, though the redhead knew better that it wasn't making matters all that much better.

It took a few minutes, but Nora was able to push her cock hard against Ruby's cervix, the spiking strike being enough to set the black haired huntress off. Her fluids squirted right out of her snatch, the dildo ruining the flow as it sprayed all over the place. Ruby heaved through her nostrils as her eyes rolled back, the orgasm she was given being the most intense feeling ever, even when it came to all of her fights as a huntress.

The two let their heads hit the ground, panting loudly from the releases they experienced. But it was clear to Nora that she wasn't finished using the two. “Okay, now that we've loosened up a bit,” she said, pausing to laugh at her own joke regarding how she stretched their holes, “I'm going to need you two to get a bit more intimate. How about a ride on the horsey?”

She pointed to a wooden 'horse', which was a triangular piece of wood that pushed out rather far, with silicone bumps ridged into the top. Both looked at it with concern, unsure of what it could entail. Their pause prompted Nora to crack her whip yet again, this time managing to get the tip against Oscar's swelled ass cheek.

The two sat atop the ridged horse, with Nora taking cuffs to their wrists to keep them behind their backs. “Now, just to make sure you two don't try to sneak off...” She then produced a short chain that she latched onto their collars, bringing their faces close enough that they couldn't pull away from each other. She then picked up a remote, pressing a button that caused the ridges to vibrate intensely against their groins. Watching the two shiver and react accordingly, Nora loved how obvious it was that the device was arousing the pair, as Ruby's fluids were dripping down the wood, while Oscar's cock began to rise back up, especially as it rubbed into his anus, taint, and balls.

“So I think both of you have something you want to say?” Nora asked. “Come ooon now, no need to hide it, there's nowhere for you two to run! You're pretty close to one another, might as well say what's on your minds!”

“I-I'll go ahead and say it!” moaned Ruby, bucking her hips as she felt a particularly high vibration against her folds. “O-Oscar, I'm in love with you! And I want you to be my boyfriend!”

“I'd...I'd like that a lot!” Oscar moaned, his cock throbbing as he shifted atop the horse to try and find comfort against his anus. “Because I love you too, Rubyyyyy!” The farm boy groaned as he bucked forward, with his cock finally bursting, his seed splattering against Ruby's body. He then leaned into the huntress, their lips locking together as they finally embraced. Nora watched on sweetly, hearing the two moan as they swapped saliva within one another.

Ruby quivered as she rocked back and forth against the ridges, with Nora believing the kiss with Oscar was what pushed her over the edge. Her fluids dribbled off the sides of the horse, dripping onto the training room floor. A huge puddle came as a result of the orgasm, with Ruby still quaking atop the device as the vibrations continued to keep her going. The redheaded mistress could see that, especially with the farmboy's rod growing after some time.

As the two continued to make out atop the vibrating station, Nora just watched on with a passionate sigh. “I knew this could work out,” she said. “it figures a little mutual torture would get you two past your silly little hangups.”

**Author's Note:**

> If you'd like to follow for more content and community, as well as updates on my content, be sure to visit me here:  
> https://discord.gg/UEYU52  
> And here: https://twitter.com/HeroicFizzer


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